-
1
-
-
0023743270
-
-
For benanomicin-pradimicin, see: a
-
For benanomicin-pradimicin, see: (a) Oki, T.; Konishi, M.; Tomatsu, K.; Saitoh, K.; Tsunakawa, M.; Nishio, M.; Miyaki, T.; Kawaguchi, H. J. Antibiot. 1988, 41, 1701.
-
(1988)
J. Antibiot
, vol.41
, pp. 1701
-
-
Oki, T.1
Konishi, M.2
Tomatsu, K.3
Saitoh, K.4
Tsunakawa, M.5
Nishio, M.6
Miyaki, T.7
Kawaguchi, H.8
-
2
-
-
0023941761
-
-
(b) Takeuchi, T.; Hara, T.; Naganawa, H.; Okada, M.; Hamada, M.; Umezawa, H.; Gomi, S.; Sezaki, M.; Kondo, S. J. Antibiot. 1988, 41, 807.
-
(1988)
J. Antibiot
, vol.41
, pp. 807
-
-
Takeuchi, T.1
Hara, T.2
Naganawa, H.3
Okada, M.4
Hamada, M.5
Umezawa, H.6
Gomi, S.7
Sezaki, M.8
Kondo, S.9
-
3
-
-
0034971898
-
-
For ohioensin B, see
-
(c) For ohioensin B, see: Dijoux-Franca, M. G.; Tchamo, D. N.; Cherel, B.; Cussac, M.; Tsamo, E. J. Nat. Prod. 2001, 64, 832.
-
(2001)
J. Nat. Prod
, vol.64
, pp. 832
-
-
Dijoux-Franca, M.G.1
Tchamo, D.N.2
Cherel, B.3
Cussac, M.4
Tsamo, E.5
-
4
-
-
20444466851
-
-
For parviflorenes, see
-
(d) For parviflorenes, see: Toume, K.; Sato, M.; Koyano, T.; Kowithayakorn, T.; Yamori, T.; Ishibashi, M. Tetrahedron 2005, 61, 6700.
-
(2005)
Tetrahedron
, vol.61
, pp. 6700
-
-
Toume, K.1
Sato, M.2
Koyano, T.3
Kowithayakorn, T.4
Yamori, T.5
Ishibashi, M.6
-
5
-
-
0028230211
-
-
For compound 4, see
-
(e) For compound 4, see: Zheng, G.; Ho, D. K. J. Nat. Prod. 1994, 57, 32.
-
(1994)
J. Nat. Prod
, vol.57
, pp. 32
-
-
Zheng, G.1
Ho, D.K.2
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6
-
-
0033519326
-
-
(a) Ohmori, K.; Kitamura, M.; Suzuki, K. Angew. Chem. Int. Ed. 1999, 38, 1226.
-
(1999)
Angew. Chem. Int. Ed
, vol.38
, pp. 1226
-
-
Ohmori, K.1
Kitamura, M.2
Suzuki, K.3
-
7
-
-
0033519228
-
-
(b) Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem. Int. Ed. 1999, 38, 1229.
-
(1999)
Angew. Chem. Int. Ed
, vol.38
, pp. 1229
-
-
Kitamura, M.1
Ohmori, K.2
Kawase, T.3
Suzuki, K.4
-
8
-
-
21244448522
-
-
(c) Ohmori, K.; Tamiya, M.; Kitamura, M.; Kato, H.; Oorui, M.; Suzuki, K. Angew. Chem. Int. Ed. 2005, 44, 3871.
-
(2005)
Angew. Chem. Int. Ed
, vol.44
, pp. 3871
-
-
Ohmori, K.1
Tamiya, M.2
Kitamura, M.3
Kato, H.4
Oorui, M.5
Suzuki, K.6
-
9
-
-
2142715741
-
-
For a review, see
-
For a review, see: Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
-
(1996)
Chem. Rev
, vol.96
, pp. 307
-
-
Molander, G.A.1
Harris, C.R.2
-
10
-
-
0037017769
-
-
For leading references, see: a
-
For leading references, see: (a) Hori, N.; Matsukura, H.; Matsuo, G.; Nakata, T. Tetrahedron 2002, 58, 1853.
-
(2002)
Tetrahedron
, vol.58
, pp. 1853
-
-
Hori, N.1
Matsukura, H.2
Matsuo, G.3
Nakata, T.4
-
13
-
-
0000516632
-
-
(d) Kito, M.; Sakai, T.; Haruta, N.; Shirahama, H.; Matsuda, F. Synlett 1996, 1057.
-
(1996)
Synlett
, pp. 1057
-
-
Kito, M.1
Sakai, T.2
Haruta, N.3
Shirahama, H.4
Matsuda, F.5
-
14
-
-
33947717423
-
-
(e) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett 1995, 158.
-
(1995)
Synlett
, pp. 158
-
-
Kito, M.1
Sakai, T.2
Yamada, K.3
Matsuda, F.4
Shirahama, H.5
-
17
-
-
0000819161
-
-
Weinheimer, A. J.; Kantor, S. W.; Hauser, C. R. J. Org. Chem. 1953, 18, 801.
-
(1953)
J. Org. Chem
, vol.18
, pp. 801
-
-
Weinheimer, A.J.1
Kantor, S.W.2
Hauser, C.R.3
-
18
-
-
33947728173
-
-
Although a mixture of dl- and meso-isomers of 2,4-pentanediol was employed, the latter preferentially took part in the reaction, giving the diastereomer 12 in 81% yield with a small amount of other diastereomers (<6% yields, The structure of 12 was assigned by 1H NMR and diagnostic NOE interactions Figure 2
-
1H NMR and diagnostic NOE interactions (Figure 2).
-
-
-
-
19
-
-
33947729419
-
-
This reaction also proceeded in the absence of a proton source, giving the product in 10% yield with a sizable amount of unidentified byproducts
-
This reaction also proceeded in the absence of a proton source, giving the product in 10% yield with a sizable amount of unidentified byproducts.
-
-
-
-
20
-
-
33947722195
-
-
254) to give 7a (trans/cis = 10:1) in quantitative yield as a colorless oil.
-
254) to give 7a (trans/cis = 10:1) in quantitative yield as a colorless oil.
-
-
-
-
22
-
-
0019454280
-
-
(a) Armstrong, R. N.; Kedzierski, B.; Levin, W.; Jerina, D. M. J. Biol. Chem. 1981, 256, 4726.
-
(1981)
J. Biol. Chem
, vol.256
, pp. 4726
-
-
Armstrong, R.N.1
Kedzierski, B.2
Levin, W.3
Jerina, D.M.4
-
24
-
-
0008224104
-
-
(c) Armstrong, R. N.; Lewis, D. A.; Ammon, H. L.; Prasad, S. M. J. Am. Chem. Soc. 1985, 107, 1057.
-
(1985)
J. Am. Chem. Soc
, vol.107
, pp. 1057
-
-
Armstrong, R.N.1
Lewis, D.A.2
Ammon, H.L.3
Prasad, S.M.4
-
25
-
-
33947732063
-
-
Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994, Chap. 14-15.
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(d) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994, Chap. 14-15.
-
-
-
-
26
-
-
0034074150
-
-
(e) Kato, H.; Ohmori, K.; Suzuki, K. Chirality 2000, 12, 548.
-
(2000)
Chirality
, vol.12
, pp. 548
-
-
Kato, H.1
Ohmori, K.2
Suzuki, K.3
-
27
-
-
33947723455
-
-
c in 17 suggested the conformation shown below (Figure 3). (Chemical Equation Presented)
-
c in 17 suggested the conformation shown below (Figure 3). (Chemical Equation Presented)
-
-
-
-
28
-
-
33947721964
-
-
Compound 16 was conformationally stable at room temperature. However, it underwent isomerization in toluene in 5 h at 90°C. The equilibrium ratio was 36:64, diequatorial/diaxial (Figure 4). (Chemical Equation Presented)
-
Compound 16 was conformationally stable at room temperature. However, it underwent isomerization in toluene in 5 h at 90°C. The equilibrium ratio was 36:64, diequatorial/diaxial (Figure 4). (Chemical Equation Presented)
-
-
-
-
29
-
-
33947723571
-
-
The stereostructure of trans-7b was determined by X-ray crystal structure analysis (Figure 5). (Chemical Equation Presented)
-
The stereostructure of trans-7b was determined by X-ray crystal structure analysis (Figure 5). (Chemical Equation Presented)
-
-
-
-
30
-
-
33947730645
-
-
The PTLC purification gave four separable diastereomers associated with relation between the 9,10-stereogenic centers in the phenanthrene skeleton and the sulfur chiral center. Oxidation of trans-7c and trans-7c′ by MCPBA led to the same compound 18. The stereostructure of 18 was determined by X-ray analysis (Scheme 9). In a similar manner, cis isomers of 7c and 7c′ were both converted into cis-19.
-
The PTLC purification gave four separable diastereomers associated with relation between the 9,10-stereogenic centers in the phenanthrene skeleton and the sulfur chiral center. Oxidation of trans-7c and trans-7c′ by MCPBA led to the same compound 18. The stereostructure of 18 was determined by X-ray analysis (Scheme 9). In a similar manner, cis isomers of 7c and 7c′ were both converted into cis-19.
-
-
-
-
32
-
-
0001272894
-
-
For leading references, see
-
(b) For leading references, see: De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157.
-
(1991)
Org. React
, vol.40
, pp. 157
-
-
De Lucchi, O.1
Miotti, U.2
Modena, G.3
-
33
-
-
0036273273
-
-
Chemical Equation Presented
-
(c) Padwa, A.; Bur, S. K.; Danca, M. D.; Ginn, J. D.; Lynch, S. M. Synlett 2002, 851. (Chemical Equation Presented)
-
(2002)
Synlett
, pp. 851
-
-
Padwa, A.1
Bur, S.K.2
Danca, M.D.3
Ginn, J.D.4
Lynch, S.M.5
-
34
-
-
33947727815
-
-
Isolation of the Pummerer product was attempted; however, it was prone to undergo hydrolysis to form the corresponding aldehyde. This aldehyde was easily dehydrated to afford 9-phenanthrene carboxaldehyde.
-
Isolation of the Pummerer product was attempted; however, it was prone to undergo hydrolysis to form the corresponding aldehyde. This aldehyde was easily dehydrated to afford 9-phenanthrene carboxaldehyde.
-
-
-
-
35
-
-
33847086035
-
-
2 in THF, see: Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
-
2 in THF, see: Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
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